WO2000034260A3 - Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group - Google Patents

Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group Download PDF

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Publication number
WO2000034260A3
WO2000034260A3 PCT/US1999/028839 US9928839W WO0034260A3 WO 2000034260 A3 WO2000034260 A3 WO 2000034260A3 US 9928839 W US9928839 W US 9928839W WO 0034260 A3 WO0034260 A3 WO 0034260A3
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
alkyl
aryl
hydrogen
heteroaryl
Prior art date
Application number
PCT/US1999/028839
Other languages
French (fr)
Other versions
WO2000034260A2 (en
Inventor
Jonathan David Bloom
Kevin Joseph Curran
Martin Joseph Digrandi
Russell George Dushin
Stanley Albert Lang
Emily Boucher Norton
Adma Antonia Ross
Bryan Mark O'hara
Original Assignee
American Home Prod
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to HU0104492A priority Critical patent/HUP0104492A3/en
Priority to IL14318399A priority patent/IL143183A0/en
Application filed by American Home Prod filed Critical American Home Prod
Priority to JP2000586707A priority patent/JP2002531555A/en
Priority to BR9916084-6A priority patent/BR9916084A/en
Priority to EP99963022A priority patent/EP1137645B1/en
Priority to CA002350833A priority patent/CA2350833A1/en
Priority to EA200100638A priority patent/EA004205B1/en
Priority to AU19346/00A priority patent/AU1934600A/en
Priority to SI9930583T priority patent/SI1137645T1/en
Priority to DE69917673T priority patent/DE69917673T2/en
Priority to KR1020017007053A priority patent/KR20010089551A/en
Priority to AT99963022T priority patent/ATE267824T1/en
Priority to NZ512135A priority patent/NZ512135A/en
Publication of WO2000034260A2 publication Critical patent/WO2000034260A2/en
Publication of WO2000034260A3 publication Critical patent/WO2000034260A3/en
Priority to NO20012833A priority patent/NO20012833L/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Quinoline Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Compounds having formula (I) wherein R1-R5 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 carbon members, aryl, heteroaryl, halogen,-CN,-NO2,-CO2R6,-COR6,-OR6,-SR6,-SOR6,-SO2R6,-CONR7R8,-NR6N(R7R8),-N(R7R8) or W-Y-(CH2)n-Z provided that at least one of R1-R5 is not hydrogen; or R2 and R3, or R3 and R4, taken together to form a 3 to 7 membered heterocycloalkyl or 3 to 7 membered heteroaryl; R6 and R7 are independently hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, or aryl; R8 is hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 members, aryl or heteroaryl, or R7 and R8, taken together may form a 3 to 7 membered heterocycloalkyl; W is O, NR6, or is absent; Y is -(CO)- or-(CO2)-, or is absent; Z is alkyl of 1 to 4 carbon atoms,-CN,-CO2R6, COR6,-CONR7R8,-OCOR6,-NR6COR7,-OCONR6,-OR6,-SR6,-SOR6,-SO2R6, SR6N(R7R8),-N(R7R8) or phenyl; G is aryl or fused bicyclic heteroaryl; X is a bond,-NH, alkyl of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, or (CH)J; J is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or benzyl; and n is an integer from 1 to 6; useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and-7, and Kaposi herpesvirus.
PCT/US1999/028839 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group WO2000034260A2 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
SI9930583T SI1137645T1 (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
AU19346/00A AU1934600A (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
JP2000586707A JP2002531555A (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpesviruses containing phenylenediamine groups
IL14318399A IL143183A0 (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpres viruses containing a phenylenediamine group
EP99963022A EP1137645B1 (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
CA002350833A CA2350833A1 (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
DE69917673T DE69917673T2 (en) 1998-12-09 1999-12-06 ALPHA-METHYLBENZYL-CONTAINING THIOHARM SUBSTANCES AS INHIBITORS OF HERPES VIRUSES WITH A PHENYLENE DIAMOND GROUP
HU0104492A HUP0104492A3 (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
BR9916084-6A BR9916084A (en) 1998-12-09 1999-12-06 Compound, pharmaceutical composition, and, processes to inhibit the replication of a herpes virus, and to treat a patient suffering from a herpes virus infection
EA200100638A EA004205B1 (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
KR1020017007053A KR20010089551A (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
AT99963022T ATE267824T1 (en) 1998-12-09 1999-12-06 ALPHA-METHYLBENZYL-CONTAINING THIOUREAS AS INHIBITORS OF HERPES VIRUSES WITH A PHENYLENEDIAMINE GROUP
NZ512135A NZ512135A (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
NO20012833A NO20012833L (en) 1998-12-09 2001-06-08 <Alpha> methylbenzyl-containing thiourea inhibitors of herpes virus containing a phenylenediamine group

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US20890298A 1998-12-09 1998-12-09
US09/208,902 1998-12-09

Publications (2)

Publication Number Publication Date
WO2000034260A2 WO2000034260A2 (en) 2000-06-15
WO2000034260A3 true WO2000034260A3 (en) 2000-09-08

Family

ID=22776519

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/028839 WO2000034260A2 (en) 1998-12-09 1999-12-06 Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group

Country Status (21)

Country Link
EP (1) EP1137645B1 (en)
JP (1) JP2002531555A (en)
KR (1) KR20010089551A (en)
CN (1) CN1165531C (en)
AR (1) AR035308A1 (en)
AT (1) ATE267824T1 (en)
AU (1) AU1934600A (en)
BR (1) BR9916084A (en)
CA (1) CA2350833A1 (en)
CZ (1) CZ20012067A3 (en)
DE (1) DE69917673T2 (en)
DK (1) DK1137645T3 (en)
EA (1) EA004205B1 (en)
ES (1) ES2221470T3 (en)
HU (1) HUP0104492A3 (en)
IL (1) IL143183A0 (en)
NO (1) NO20012833L (en)
NZ (1) NZ512135A (en)
PT (1) PT1137645E (en)
WO (1) WO2000034260A2 (en)
ZA (1) ZA200104376B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6844367B1 (en) 1999-09-17 2005-01-18 Millennium Pharmaceuticals, Inc. Benzamides and related inhibitors of factor Xa
DK1259485T3 (en) 2000-02-29 2006-04-10 Millennium Pharm Inc Benzamides and related inhibitors of factor Xa
WO2002016318A1 (en) * 2000-08-21 2002-02-28 Pacific Corporation Novel thiourea derivatives and the pharmaceutical compositions containing the same
JP4360885B2 (en) 2003-11-28 2009-11-11 富士フイルム株式会社 Method for producing aromatic amine compound having alkylthio group
WO2007024754A1 (en) * 2005-08-22 2007-03-01 Amgen Inc. Bis-aryl urea compounds for the treatment of protein kinase-mediated diseaes
ES2382055T3 (en) 2006-11-02 2012-06-04 Millennium Pharmaceuticals, Inc. Methods for synthesizing pharmaceutical salts of a factor Xa inhibitor
CN112807294B (en) * 2019-11-18 2023-09-05 武汉大学 Application of acyl thiourea compound in preparation of medicines for treating or preventing herpes simplex virus type I infection
CN115433093A (en) * 2022-09-26 2022-12-06 无锡双启科技有限公司 Preparation method of 3-chloro-4-trifluoromethylaniline

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0462933A1 (en) * 1990-06-18 1991-12-27 Sandoz Ltd. Novel N-benzyl-N1-phenyl and -phenalkyl-thioureas
WO1996025157A1 (en) * 1995-02-17 1996-08-22 Smithkline Beecham Corporation Il-8 receptor antagonists
WO1997011052A1 (en) * 1995-09-21 1997-03-27 Novartis Ag Urea derivatives and their use as analgesics and antiinflammatory agents
WO1997040028A1 (en) * 1996-04-23 1997-10-30 Vertex Pharmaceuticals Incorporated Urea derivatives as inhibitors of impdh enzyme

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0462933A1 (en) * 1990-06-18 1991-12-27 Sandoz Ltd. Novel N-benzyl-N1-phenyl and -phenalkyl-thioureas
WO1996025157A1 (en) * 1995-02-17 1996-08-22 Smithkline Beecham Corporation Il-8 receptor antagonists
WO1997011052A1 (en) * 1995-09-21 1997-03-27 Novartis Ag Urea derivatives and their use as analgesics and antiinflammatory agents
WO1997040028A1 (en) * 1996-04-23 1997-10-30 Vertex Pharmaceuticals Incorporated Urea derivatives as inhibitors of impdh enzyme

Also Published As

Publication number Publication date
KR20010089551A (en) 2001-10-06
JP2002531555A (en) 2002-09-24
NO20012833L (en) 2001-08-02
CN1329608A (en) 2002-01-02
NZ512135A (en) 2003-12-19
DK1137645T3 (en) 2004-08-09
WO2000034260A2 (en) 2000-06-15
CA2350833A1 (en) 2000-06-15
IL143183A0 (en) 2002-04-21
DE69917673T2 (en) 2005-06-09
EA004205B1 (en) 2004-02-26
NO20012833D0 (en) 2001-06-08
CN1165531C (en) 2004-09-08
ZA200104376B (en) 2002-08-28
AR035308A1 (en) 2004-05-12
CZ20012067A3 (en) 2001-10-17
ES2221470T3 (en) 2004-12-16
DE69917673D1 (en) 2004-07-01
AU1934600A (en) 2000-06-26
EA200100638A1 (en) 2001-12-24
BR9916084A (en) 2001-09-04
ATE267824T1 (en) 2004-06-15
EP1137645A2 (en) 2001-10-04
HUP0104492A2 (en) 2002-04-29
HUP0104492A3 (en) 2002-12-28
PT1137645E (en) 2004-09-30
EP1137645B1 (en) 2004-05-26

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